Cns depressant amino-oxazoline compounds, methods, and compositions

ABSTRACT

WHEREIN X is oxygen, sulfur or methylamino; R is hydrogen or alkyl; R&#39;&#39; is hydrogen, alkyl, alkoxy, alkylthio, dimethylamino, fluorine, chlorine or bromine; R&#39;&#39;&#39;&#39; is hydrogen or alkyl; R&#39;&#39;&#39;&#39;&#39;&#39; is hydrogen or alkyl. Typical is 2-(4-thiochromanylamino)-2-oxazoline useful as a central nervous system depressant.   Amino-oxazolines useful as central nervous system depressants having the formula:

United States Patent 72] Inventor George Levitt Wilmington, Del.

[2| Appl. No. 22,027

[22] Filed Mar. 23, 1970 [45] Patented Nov. 30, 1971 [73] Assignee E. I.du Pont de Nemours and Company Wilmington, Del.

Original application June 12, 1967, Ser. No. 646,154, now Patent No.3,509,170. Divided and this application Mar. 23, 1970, Ser. No. 22,027

[54] CNS DEPRESSANT AMlNO-OXAZOLINE COMPOUNDS, METHODS, AND COMPOSITIONSPrimary Examiner Donald G. Daus All0rney-Don M. Kerr ABSTRACT:Amino-oxazolines useful as central nervous system depressants having theformula:

R /R X o- -ou-l ll I s .v C.

R" R N (IL- II -NC Q X v R" R N-(Jll:

wherein X is oxygen, sulfur or methylamino; R is hydrogen or alkyl;

R is hydrogen, alkyl, alkoxy, alkylthio, dimethylamino. fluorine,chlorine or bromine;

R" is hydrogen or alkyl;

R' is hydrogen or alkyl.

Typical is 2-(4-thiochromzmylamino)-2-oxazoline useful as a centralnervous system depressant.

CNS DEPRESSANT AMINO-OXAZOLINE COMPOUNDS, METHODS, AND COMPOSITIONSCROSS-REFERENCE TO RELATED APPLICATION This application is a divisionalof my application Ser. No. 646,154, filed June 12, 1967, now U.S. Pat.No. 3,509,170.

BACKGROUND OF THE INVENTION The following applications relate to variousclasses of oxazolines generally useful as pharmaceuticals: Harvey, Ser.No. 52l,746, filed Jan. 19, 1966, now U.S. Pat. No. 3,453,284; Levitt,Ser. No. 479,054, filed Aug. 10, 1965, now U.S. Pat. No. 3,499,083;Levitt, Ser. No. 479,055, filed Aug. 10, 1965, now U.S. Pat. No.3,499,084; Harvey, Ser. No. 468,999, filed July 1, 1965; Harvey, SerialNo. 348,290, filed Feb. 28, 1964, now abandoned; Harvey, Ser. No.313,756, filed Sept. 30, 1963, granted as U.S. Pat. No. 3,432,600.

The present invention is directed to a new class of oxazolines havingcentral nervous system depressant effect.

SUMMARY OF THE INVENTION This invention relates to amino-oxazolines.More specifically this invention refers to compounds of the X is oxygen,sulfur or methylamino;

R is hydrogen or alkyl of one through four carbon atoms;

R is hydrogen, alkyl of one through four carbon atoms, alkoxy of onethrough four carbon atoms, alkylthio of one through four carbon atoms,dimethylamino, fluorine, chlorine, or bromine;

R" is hydrogen or alkyl of one through four carbon atoms;

R is hydrogen or alkyl of one through four carbon atoms;

Preferred because of excellent central nervous system depressantactivity at low use rates are those compounds of formulas l) and (2)wherein X R are hydrogen and R is alkyl, alkoxy or hydrogen. The mannerand process of making and using this invention is 4 described in U.SvPat. No. 3,509,170, U.S. Class No. 260, Subclass No. 307 issued Apr. 28,1970, the disclosure of which is hereby incorporated by reference.

lclaim:

l. A compound of the formula:

O-GH:

group consisting of hydrogen and group consisting of hydrogen and isoxygen or sulfur; R, R" and W105) UNITED STATES PATENT OFFICECERTIFICATE OF CORRECTION Patent No. L62)-l 4392 Dated November 30, 1971Inventor(s) George Levitt It is certified that error appears in theabove-identified patent and that said Letters Patent are herebycorrected as shown below:

In Column 2 at line 7, delete "R" and insert in place thereof R" 5 atline 11, delete R" and insert in place thereof R" 5 at line &3, delete"R" and insert in place thereof R" Signed and sealed this 9th day of May1972.

ISEAL} Lttest:

EDWARD M.FLE'I'CHER,JR. ROBERT GOTTSCHALK \ttesting Officer Commissionerof Patents

2. A compound according to claim 1 which is2-(1,2,3,4-tetrahydro-1-methyl-4-quinolinylamino)-2-oxazoline.